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Method for synthetizing 2,3-disubstituted dihydrobenzofuran

A benzodihydrofuran and disubstituted technology, applied in the field containing dihydrobenzofuran, can solve the problems of poor chemical selectivity and stereoselectivity of products, harsh reaction conditions, expensive reaction reagents or catalysts, etc., and achieve complete conversion of raw materials. , the effect of easy availability of raw materials and convenient separation

Inactive Publication Date: 2014-01-15
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Because most of the reaction conditions used in the synthesis of 2,3-substituted chroman dihydrofurans are relatively harsh, the reaction reagents or catalysts are expensive, and the resulting products have poor chemoselectivity and stereoselectivity, which prevents the widespread application of these methods

Method used

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  • Method for synthetizing 2,3-disubstituted dihydrobenzofuran
  • Method for synthetizing 2,3-disubstituted dihydrobenzofuran
  • Method for synthetizing 2,3-disubstituted dihydrobenzofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Synthesis of compound 3a

[0031]

[0032] Add substituted phenol 1a (1.0 mmol), sulfur ylide 2a (1.2 mmol), and cesium carbonate (2.5 mmol) into a reaction flask protected by nitrogen, and then add 4 ml of dry dichloromethane. After 12 hours of reaction at room temperature, saturated sodium thiosulfate solution was added to quench the reaction. After standing for liquid separation, the aqueous layer was extracted three times with dichloromethane (3×5 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and silica gel column chromatography was used to obtain the product compound 3a.

[0033] tran-Ethyl 3-phenyl-2,3-dihydrobenzofuran-2-carboxylate(3a). White solid, melting point 59-60°C, yield 99%, 1 H NMR(400MHz, CDCl 3 )δ7.35-7.20(m,6H), 7.00(dd,J=7.4,4.1Hz,2H), 6.91(t,J=7.4Hz,1H), 5.03(d,J=6.6Hz,1H), 4.81(d,J=6.5Hz,1H), 4.29(ddd,J=12.5,7.5,2.8Hz,2H), 1.31(t,J=7.1Hz,3H); 13 C NMR(100MH...

Embodiment 2

[0034] Example 2: Synthesis of compound 3b

[0035]

[0036] Add substituted phenol 1b (1.0 mmol), sulfur ylide 2a (1.2 mmol), and cesium carbonate (2.5 mmol) into a reaction flask protected by nitrogen, and then add 4 ml of dry dichloromethane. After 12 hours of reaction at room temperature, saturated sodium thiosulfate solution was added to quench the reaction. After standing for liquid separation, the aqueous layer was extracted three times with dichloromethane (3×5 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and silica gel column chromatography was used to obtain the product compound 3b.

[0037] tran-Ethyl 3-ethyl-2,3-dihydrobenzofuran-2-carboxylate(3j). Colorless liquid, yield 77%; 1 H NMR(400MHz, CDCl 3 )δ7.16(t,J=7.8Hz,2H),6.91-6.88(m,2H),4.82(d,J=5.4Hz,1H),4.33-4.18(m,2H),3.50(dd,J =12.7,5.7Hz,1H),1.81(ddd,J=21.4,10.7,6.2Hz,2H),1.29(t,J=7.1Hz,3H),1.03(t,J=7.4Hz,3H); 13 C NMR(100MHz, CDC...

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Abstract

The invention discloses a method for synthetizing 2,3-disubstituted dihydrobenzofuran. Kinds of substituted 2,3-disubstituted dihydrobenzofurans can be obtained from simple ylide and substituted phenol by reactions under an alkali catalytic condition. The method disclosed by the invention is simple and practical in operation, available in raw materials, high in yield, and good in diastereoselectivity.

Description

Technical field [0001] The invention relates to a method containing dihydrobenzofuran, specifically a method for synthesizing 2,3-disubstituted benzodihydrofuran Background technique [0002] Compounds containing dihydrofuran rings are widely present in nature and account for a considerable proportion of natural products isolated and identified. Most furan alkaloids show important biological activities, such as anticancer marker enzymes and quinone reductases [Document 1: F. Bertolini, M. Pineschi, Org. Prep. Proced. Int. 2009, 41, 385-418.] , Fungicides, insecticides [Document 2: B. Vinosha, S. Perumal, S. Renuga, AI Almansour, Tetrahedron Lett. 2012, 53, 962-966], and can treat multidrug resistance [Document 3: F. Baragona, T. Lomberget, C. Duchamp, N. Henriques, EL Piccolo, P. Diana, A. Montalbano, R. Barret, Tetrahedron 2010, 67, 8731-8739] etc. Therefore, it has important and very wide applications in the fields of agriculture and medicine. At present, there are many meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79C07D307/82C07D307/85
CPCC07D307/85
Inventor 周永贵段英陈木旺陈庆安
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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